Holiday Itinerary

I learned as a tourist to many places around the world, the best thing to do is stroll and take in the sights. Even as a New Yorker, I can easily spend 2 hours in Central Park, a place I have visited 100s of times over the years. This itinerary is meant to be a guide, not a “YOU MUST DO THIS.” Take your time and enjoy. In fact, this can take you two days — you know what’s best. Whether you are traveling alone or with others, this plan can get you started.

Breakfast: When you get up

No matter where you stay you can find quick bites and bagels around you.

Sarabeth’s Central Park South – 40 Central Park South, Located in: 40 West 59th Street Condominium,
Start your day with a cozy, classic NYC breakfast — lemon ricotta pancakes, eggs Benedict, and fresh pastries. Steps from Central Park, it’s the perfect morning fuel.
Want a quicker start to the morning? Try H&H bagels which I LOVE. (Columbus 84th Street)
Zuckers (Columbus and 72nd)

Columbus Avenue Stroll – (90 minutes)
Walk west to Columbus Circle, then north on Columbus Avenue (59th–75th Street) to enjoy boutique shops, bakeries, and charming holiday window displays.

Some Shops on Columbus Avenue:

Levain Bakery (351 Amsterdam Ave, near Columbus)
Paper Source (410 Columbus Ave)
Theory (210 Columbus Ave)
The North Face (210 Columbus Ave)
Rituals (420 Columbus Ave)
Flying Tiger Copenhagen (128 Columbus Ave)
Zabar’s (2245 Broadway at 80th Street)

OR, visit the upscale Mall The shops at Columbus Circle. This is quite close to Sarabeth’s Kitchen. So depending on what you want to do mall or stroll.

Central Park- (90 minutes): Enter at 72nd Street and Central Park West, near Strawberry Fields. Walk south through the park.

Top Highlights:
Strawberry Fields / Imagine Mosaic
Bow Bridge
Bethesda Terrace & Fountain
The Mall and Literary Walk
The Pond & Gapstow Bridge

Tips: Avoid horse carriages and pedicabs — walking is safer, cheaper, and more enjoyable.

Lunch at The Loeb Boathouse – (90 minutes)
Finish your park walk with a relaxing lunch at The Loeb Boathouse, a true NYC icon overlooking the lake. Make reservations in advance, as this is a favorite for both locals and tourists. Try their crab cakes or the Boathouse burger while you take in the view.

Side Trip: The Metropolitan Museum of Art – (2 -3 hours) The most magnificent collection of exhibits. For me this is a 2 to 3 hour stop, which is why I say that this is a very packed Itinerary and you probably won’t get to everything if you are doing it right.

Fifth Avenue Walk – ( 2 – 3 hours)

Walk south along 5th Avenue, experiencing the festive holiday displays, shopping, and iconic NYC sites.
Fifth Avenue Highlights:
FAO Schwarz – Shopping and iconic store
Bergdorf Goodman – Upscale shopping
Louis Vuitton- Just a photo op of the building unless you go in.
Nike Flagship Store (custom sneakers; allow time if stopping)
St. Patrick’s Cathedral – 5th Ave between 50th and 51st Street. Stop inside to admire the neo-Gothic architecture, stained-glass, and festive decorations.
Rockefeller Center – tree THERE ARE HUGE CROWDS and ice rink (reservation suggested) (this can be 2 hours alone if you skate and stop and shop)

Side Trip: Top of the Rock ( 1 hour)
Location: 30 Rockefeller Plaza, between 49th–50th Streets & 5th–6th Avenues. Best at night for sunset views. Also crowded. Purchase timed tickets in advance online to avoid lines. The best times are late afternoon for sunset or evening for city lights.

Directions: From Rockefeller Center Plaza, head to the entrance at 50th Street between 5th & 6th Ave. Use the security checkpoint to access the observation deck elevators. Decks are outdoors with panoramic views of the Empire State Building, Central Park, and Midtown Manhattan.

Side Tour – Grand Central Station -(90 Minutes)
Walk east to Grand Central Terminal. The closest entrance is Vanderbilt and 45th Street.
Things to Do:

Oyster Bar & Restaurant
Grand Central Holiday Market (Vanderbilt Hall)
Whispering Tunnel –
The main hall with a view of the “sky” – photo op

Side trip: visit Summit One Vanderbilt (steps from Grand Central) for immersive city views. I think you should pick either the top of the rock, or Summit One. Mirrors, glass floors, and skyline panoramas, particularly magical at sunset and early evening. 45 East 42nd Street.

Bryant Park Winter Village – 1 – 2 hours
Walk west to Bryant Park. Ice skating (PRICEY!!), the best gift shops, and festive food.

Dining Options:

Bryant Park Grill (reservations recommended)
Winter Village casual options TikTok reccos – I can’t eat all of them: PetiscoBrazuck Brazilian Cheese Breads, Last Crumb, Crispy Chick, Buttermee Pancakes, Breezy Hill Orchard, Pickle Me Peter, Ovelia, Gunthers, 12 Chairs, Fresh Schnitzel, Babka Bailout

Holidayish Bars (not in the area)